Captain Jane
by LovelySheree
Summary: After escaping her Brenner and his factory, Jane dedicates her life to putting an end to greedy industries such as his. She assumes the Wheeler Family's iron business is no different and makes plans to end it. But there's one problem: the business' inherent, Micheal Wheeler. (Or El is a pirate who captures Mike but things don't go as planned. This story is very hard to summarize)
1. Chapter 1

**Welcome to my newest story! It's a Pirate AU which sounds dumb, but it's been really fun to think about and write. So... yup. Here goes nothing. I hope you enjoy!**

* * *

Chapter 1

Mike stands at the edge of a large ship, leaning overboard to watch the waves crash against the wooden planks. All things considered, it's a beautiful day. There's a perfect sea breeze, gently brushing past his hair, and the sky is as blue and endlessly stretching as ever. A day like today is the definition of pleasant; however, Mike feels anything _but_. He absolutely _hates_sea travel. As the boat rocks back and forth, he fights the urge to vomit. Great… only one day in and he already feels sick to his stomach.

But it isn't just the seasickness that spurs on his sour mood. It's _everything. _He has been dreading this trip since the beginning of the year when his father sprung it on him.

_"Michael, we have a potential partnership in the southern colonies," _his father had told him on a particularly cold January morning. Theodore Wheeler, proud inheritor of his father's (Mike's grandfather's) wealth in the iron business. He wore the same expression as he wore every other day. Suppressed boredom with a twinge of quiet, but deeply settled resentment. Although the complete void that was Mike's father left much to be desired in terms of fatherly love, he couldn't blame him. If there was anyone else who understood the absolute _bore _of recording the financial transactions of pots and pans and anything else iron, it was Mike.

_"I assume you would like me to stay here and manage the books, then?" _he had replied, not thinking much of it at the time.

_"Actually,_you_will be going… as the heir of the business," _his father had clarified, _"You leave come the beginning of summer."_

And then came the beginning of summer and Mike had packed his bags and loaded himself onto the first ship to the southern colonies. He huffs a breath of air from his lungs, wishing desperately he was anywhere else. He never liked the iron business. Or any business for that matter. But if you were to ask Mike what he _did _like to do, he probably would be able to say. Not even _he _knew, because his entire life he's been preparing to take over his father's company. It's not like there's another option, so there's no point in dreaming about one. He blinks slowly and lets out a pitiful groan as he stands up, leaning away from the water below.

"You seem chipper," he hears a voice behind him.

Mike turns around to see Lucas Sinclair, a longtime friend and brother, wearing a sarcastic smile. The Sinclair's were a family that had worked for Mike's grandfather years ago. They were a part of his father's "inheritance," though Mike always considered them family. Hell, Mike considered the Sinclair's to be his family more than his actual biological one. He spent many days and nights escaping his house and joining the Sinclair's in their small moments of free time, unbeknownst to his parents.

"I get that from my father," Mike says, turning back to the ocean.

He sees Lucas join him at his side out of the corner of his eye, watching him lean onto the wooden railing. "Funny," Lucas remarks, "You get that from you father, too?"

Mike snorts, "I'm afraid my wit comes from years of living a cynical life." He steps away from the railing, turning around and slumping against it, allowing his long limps to fold beneath him in a tangled heap as he lowered himself to the floorboards. He leaned to the side, letting out a small, strangled grunt as he tugged something out of the bag that hung at his hip.

Lucas rolled his eyes, scoffing as he watched Mike pull out an old, well-used book. "Not that damned thing," Lucas shook his head, "How many times have you read that, anyway?"

Mike glanced up at his friend before turning back to his book. "I've honestly lost count," he said, squinting at the pages.

"Isn't it boring to read the same thing over and over again? Where's the fun in that, huh? There's no mystery or surprise," Lucas said, hunching over the railing. "Besides, isn't that the _point _of the book? It's about pirates and treasure hunting, right? They solve a mystery, find the treasure, become filthy rich…"

"Sure, it's about mystery and all, but… I don't know," Mike turns the first page, half ignoring Lucas already. "I just like reading it, okay?"

"Good luck convincing him to put it down," a familiar voice pulls Mike from his reading for a brief moment. William Byers accompanied by Dustin Henderson, two of Mike's closest friends. The three of them attended the same school together throughout their entire childhood. That is, until Will's dad up and left on day. After that, Will had to stay home from school so that he and his brother could earn enough money for themselves and their mother. Although it was a terrible circumstance, Will and Mike became closer because of it. Will was able to find a temporary job working for Mike's father, managing the less important numbers alongside Mike. "I don't think I've ever seen him without it," Will says with the beginnings of a wry smile in his eyes.

"I read it, and it was good, but not worth reading every goddamn day," Dustin retorts, looking Mike up and down. "Shit, you look as white as a ghost," he observes.

Mike sighs, wishing he were someone quieter. And steadier. And just _not here. _"I'm feeling a bit nauseous," he admitted, "I'm not too good with boats."

"Or business deals," Lucas laughs, earning a harsh nudge in the shins from Mike below, "Ow—hey!"

"Why is it that I'm suddenly regretting bringing you guys along?" Mike asks dryly, closing his book and tucking it away.

Dustin grins down at him, "Aw, come on, Mikey. What would you do without us?"

Mike let his head fall against the bulwark with a soft thud. "I'd be _reading _for one. I can't concentrate with all of your guys' blabbering," he says.

"You have that book memorized like the back of your hand," Lucas scoffs, "Don't blame us for not being able to enjoy your book."

Lucas was right, they weren't at fault for Mike's inability to concentrate. Or rather, concentrate on what he'd _prefer_to concentrate on. The idea of taking over his father's company had always been in the back of Mike's mind, sure, but now it's starting to become real. He's on an important business trip as "the heir of the company." He shudders at the thought. His father's business is safe and successful, not to mention Mike knows how to manage it fairly well. Whether he _enjoys _managing it or not is another story. Then again, Mike can safely assume his father doesn't enjoy it either, but he's done it his entire life.

_"It's a man's duty to find an honest job and do it well. It doesn't matter if you enjoy it or not," _he hears his father's voice ring in his head. _I wonder how many times he had to tell himself that, Mike _wonders, watching his friends banter back and fourth around him. Lucas leans over and smacks Dustin's forehead for something he said, but Mike's not really listening to what they're all bickering about.

Will turns to him, probably noticing his silence. "Do you want something to ease your stomach?" Will asks, taking a step away from Dustin and Lucas and towards Mike.

Mike shakes his head, "No, it's not unbearable."

"Well if it's not your stomach, what's eating at you?"

Mike give's Will a flat look. "You know _exactly_what's eating at me," he says.

"Well sure, but I prefer not to assume things," Will says, plopping himself down next to Mike. "Plus, it may feel good to get it off your chest."

Mike sighs and stands up, closing his eyes and pinching the bridge of his nose. "I think I'm just gonna go below deck into our quarters… maybe rest will do me some good." he says, making his way towards the stairs that lead to the lower portion of the ship.

He can feel Will, Dustin and Lucas all collectively watch him leave, but he tires his best to ignore them. He's _tired, _he tells himself. Whether that holds much truth or not, Mike doesn't care to dwell on. Because right now, he _did _feel tired. As he walks towards the small room where he and his friends are all going to cram in on this hellish voyage, the idea of falling into a blank, blissful sleep is a wonderful one.

Of course, the universe seems to disagree. Because the moment Michael Wheeler, not-so-proud inheritor of hisfather's business, laid down on his cot, the entire ship erupts in sudden commotion.

Over the loud and stomping footsteps above, he barely makes out a panicked cry.

"Pirates!"

Jane sat in her quarters mulling over her crew's recent reports. Most were the routes and schedules of simple shipping vessels, carrying local businesses' cargo from one port to the next. The pirate in her was excited at all the opportunities to steal back from the greedy, profit-minded businesses, but that wasn't what she and her crew were currently after. Well, at least they weren't after just _any_business.

The Wheeler Family Iron, known for their extremely affordable iron output. Of course, it was at the heavy cost of slave labor. Sure, most businesses used slave labor, but at the rate the Wheeler's family business was growing, she feared their slave labor would only grow as well. When she received word that they were reaching out to the southern half of the colony, she knew she needed to step in. If their business gained enough partnerships, there's no telling how many lives would be extorted.

Yes, Jane was a pirate. Her profession was thievery. However, she didn't consider herself to be a true thief. Sure, she wasn't above petty theft every now and then, but the true criminals were the ones behind the scenes. The ones who stop at nothing in the pursuit of wealth—even when they're plenty wealthy already.

The_true _thieves were greedy businesses. Businesses like The Wheeler Family Iron.

"Captain Jane," she hears a voice call her from outside her door, pulling her from her thoughts.

"Come in, Max," she says, and the door opens, "Is something wrong?" she looks up to see her second-in-command, a fiery red-head with a personality to match, entering her quarters.

"We've got our target," Max says, grinning as she crosses her arms over her chest. "In record time, I might add."

Jane nods facing Max with a grin of her own. "Tell Kali to ready the cannons," she says while standing up. "We've got thieves to catch."

* * *

**Hope you guys enjoyed! This is posted on AO3 as well if you follow me on both platforms. Also go ahead and check out my Tumblr lovelysheree if you'd like to see my fanart or chat or whatever .**


	2. Chapter 2

**Yep, the first two chapters are back to back updates! (Not all will be, it's because I had both chapters already written... RIP my updating schedule lol)**

* * *

Mike jumps from his bed, watching dust fall from the ceiling in feathery streams. The boat shakes with commotion as he watches a young cabin boy race past his quarters, yelling at everyone below deck. "Remain calm and stay in your rooms! No passenger is to go above deck!" he yells.

"What in the…" Mike mumbles, looking out his doorway to see another cabin boy leading—or _trying _to lead—a large group of panicked men and women to their quarters. He tries to make out any of his friends in the blur of people, but as they all rush past his doorway, there was no sign of Will, Dustin or Lucas. He still hears thundering footsteps and voices coming from above deck, so he assumes they must still be up there.

A man screams suddenly, directly above Mike's quarters. "D-don't shoot!" the man begs.

Mike looks up and peeks through the cracks the ceiling to see the boots of the hefty man, begging for his life. Across from them stood another pair of smaller, thinner boots. Mike would've thought it was another cabin boy judging by the shoe size, but the voice catches him completely off guard.

"I don't find pleasure in harming people," a soft, yet assertive voice states. It's a woman's voice. "And all I need is some information," she continues.

Mike couldn't make out her appearance through the cracks very well. He could only see her shoulder-length brown hair and her long coat, both swaying with each step she took forward. On top of her head she wore an angular hat—one Mike recognizes from the cover of his book. _A pirate, _he thinks as his heartrate picks up, _A real life pirate…_

"I-I'm afraid the information of this ship is confidential," the man says.

The woman raises her arm and Mike hears the loud _click _of a hammer cocking a pistol. "What about the information of the passengers?" she asks, her voice dipping lower.

"They have their right to privacy," the man says, taking a step back.

"I agree, privacy is a natural right," she replies, lowering her arm, "You seem like an honorable man, your captain is lucky to have a second-in-command like you." She added, her voices lifting to a casual tone. Mike felt a sigh of relief leave his body in a shaky breath as he watched the scene unfold above him (or as best as he could see through the floorboards). "However, I'm afraid that's not the answer I'm looking for," Mike's breath hitches in his throat as he watches the woman's arm lift up and the click of a cocked pistol pierces his ears again.

_"__Mike!_" Mike whips around at the sound of Lucas' harsh whisper from the doorway. "Come on, we've got a boat ready. Will and Dustin are already there and ready to escape," he says, keeping his voice low. There are still people running through the quarters, occasionally rushing past Lucas, but the majority had already found their rooms and hidden.

Mike frowns at Lucas, "_Escape? _What are you talking about?"

"Are you daft? _Pirates _are on the ship and they've already gotten the Captain," Lucas whispers, "If we don't leave now, we'll all likely be dead in a few hours… or worse." He waves Mike towards him, "Now come _on_!"

Mike shakes his head, regaining his senses. "Right, right," he mutters nervously, looking around the room for his belongings. He grabs his bag and slips his hat on his head, knowing his hair—frizzy and curly from the ocean air—is poking out over his ears. But clearly this is not the time for dwelling on appearances. "Okay let's—"

"_Hurry,_" Lucas hisses impatiently, cutting Mike's sentence short. He grabs Mike's shoulders and pushes him up the stairs towards the deck. "They're waiting for us towards the back of the ship," Lucas says in a rush.

Mike shoves Lucas' hands off his shoulders, "O_kay,_I'm hurrying as fast as I can," he says. As they approach the door to the deck, they slow down and peek out. Mike's eyes go wide in astonishment. There are too many people to count, all wielding swords and pistoles and weapons alike, fighting each other.

"Shit!" Mike jumps back and ducks down as a bullet hits the wooden frame of the doorway he was just standing in. As to whose gun it was fired from, Mike has no clue. With all the chaos, it could've been this ship's crew who almost just shot him.

Mike looks back to Lucas who's backed against the wall as well, "You okay?" he asks Lucas.

Lucas nods, then looks towards the door. "We should make a run for it sooner rather than later. Knowing Will and Dustin, they've already found themselves in a load of trouble."

Mike nods, peeking out the door once more. "They probably won't notice if we sneak pass with all of the commotion," he muses.

"Well then sneak away—I'm right behind you." Lucas says, and Mike can hear the nervous frustration growing in his friend's voice.

He manages to stay low to the ground, though his long limbs make the process quite clumsy. By now, they are far enough away from the gunfire and fighting that they aren't ducking under stray bullets. Without the immediate threat of being killed on his mind, Mike finds himself wondering _why _this is all happening. Is there a criminal on the boat? That's what the woman had said earlier, the one he saw through the floorboards.

_She wanted the name of a passenger, _he remembers. He can still hear the sound of her gun clicking in an unspoken threat that rings endlessly in his ears. Even the thought of murder makes him want to curl into himself. Taking someone's life… Well, that's a lot to have on your conscience and Mike's is already full enough.

He shakes himself out of his thoughts. _Now is not the time to be thinking about that, _he thinks. "Where did you say Dustin and Will are?" Mike asks over his shoulder, still having to speak over the loud commotion.

"Just behind those boxes," Lucas nods ahead towards a tall pile of crates tied securely to the deck. "There's a lifeboat they managed to secure over there," he finishes.

Mike follows Lucas' gaze, "Okay—" but the word freezes on his lips. He hears a loud _thump _behind them.

"Don't move," a voice commands. It was a voice Mike recognized.

He turns around to see a familiar figure wearing a long coat and the signature pointed hat of a pirate. It's the woman from earlier. _Pretty, _he thinks,and he curses himself for noticing.

This time she doesn't hold her gun, instead she points the tip of her sword at them, but Mike can make out the gun strapped securely in its holster at her hip. He watches as Lucas flinches backwards and she edges her sword closer. "Don't. Move," she repeats with eyes as cold as stone.

"Please, let us go," Mike hears himself talk, but he can barely process his own words. His heart hammered dangerously in his chest. This woman… What had she done with the Captain and his First Mate? "We don't want to cause any trouble," he says nervously.

The woman's eyes meet his with an anger he's unprepared for. "I'm afraid it's too late for that," she says as if it were the truest thing she had ever spoken.

"T-too_late? _We haven't caused any trouble yet! _You're _the ones who invaded our ship and caused the trouble!" Lucas yells indignantly. And although he has a point, Mike has never wanted to slap his friend so badly. Now is _not _the time for being right.

However, the woman seems practically unfazed by Lucas' retort. In fact, she barely even acknowledges his statement. "This doesn't concern you," she simply states, sparing a glance at Lucas before flicking her eyes right back to Mike. "What is your name?" she asks, and while it sounds like a question, Mike knows it's anything _but._

"Mike," the name slips from his mouth, "M-Michael Wheeler."

"Correct me if I'm wrong, _Michael, _but you're aboard this ship for business purposes, yes? You run your father's company—your family's company," she says, narrowing her eyes.

Mike nods numbly. What did _any _of this have to do with his father's business? Did their competition hire pirates to take him out? That seems a bit dramatic for simple business competitors. Besides, they've never had any issues with competitors in the past, so why now?

Mike watches her look up from him and tilt her head to the side to signal someone. Mike turns around to see two other women, both holding swords to Dustin and Will's necks. "You and your friends will be coming with us," she says, her cold eyes finding his again.

"Me and my—_what? _What the hell is going on?" Mike's so confused he feels like screaming, but the question barely leaks out of him. He feels like a damp and tightly rung towel with only a few more drops of water left to offer.

The woman takes a step closer to him, letting her sword fall to her side. "You run a greedy, tainted business. I make it my sole priority to take pigs like you out," she explains, "And the Wheeler family name soaks in innocent blood."

"_'__Innocent blood?' _What are you _talking _about!?" Mike asks, his heart beating wildly in his chest. _She doesn't know. She doesn't—she _can't _know,_he reminded himself, _no one knows. _

"You may not take lives, but you _do _take livelihoods. You don't care what happens or how it happens so long as you gain a hefty profit," she says, and he can see her knuckles turn white from gripping her weapon tightly. "Are you aware _how _your business gains its profit, _Mr. Wheeler_?"

"I—I just run numbers—I—we—we're _clean, _I swear!" he said, pushing himself off the ground to stand up while keeping his hands in the air. _No one knows…_

"Are you willing to bet your friend's life on that?" he hears one of the women speak behind him. He turns to see that it was the one with the darker hair that was shaved on one side and tousled messily on the other. She tightens her grip on Will's shoulder and edges her knife closer to his throat.

Mike watches in horror as Will tightly shuts his eyes. "Stop! Stop! They don't have _anything_to do with this, right!? You said it yourself!" he turns back towards the first woman, the one in the pirate hat. "This doesn't concern them," he says slowly. He can see a brief conflict swim in the woman's honey-brown eyes, and he wonders how such warm eyes could feel so cold. "Please," he speaks cautiously, "Let them go. They can take the lifeboat and go home to their families."

"M-Mike no! They don't know what they're talking about—you haven't done anything wrong!" Dustin yells from behind him.

"Don't do this," he hears Will plead.

"You said, 'the Wheeler family name soaks in innocent blood,' and yours will to if you take them. It's me you want, right? Leave them out of this," Mike bargains. If his friends got wrapped up in this all because of _him... _well, he wouldn't be able to live with himself.

Mike hears the dark-haired woman speak up and walk towards them, "Jane, don't listen to him—"

_Jane,_Mike thinks, his dark eyes meeting her brown ones. "That's very noble of you, Mr. Wheeler," the woman—_Jane_—speaks, ignoring the dark-haired woman that now stood at her side. "As a reward for your selflessness," she says while nodding to the redhead who now held Dustin and Will singlehandedly, "I'll allow them to leave if you promise to come willingly."

Mike can see Lucas look up from the ground at him, "Seriously Mike," he says quietly, "These women are crazy, they don't know what they're talking about—"

"Deal," Mike says, ignoring Lucas. "Take me and let them go."

Jane nods, pointing her sword at Lucas who still sits on the ground. "Stand up," she instructs.

Lucas quickly stands up, looking at Mike as he walked past him towards Dustin and Will who now stood by the lifeboat. "Mike…" he tries to get his attention, but Mike kept his eyes glued to Jane's. He can't risk looking away. He might lose his nerve if he does.

He can hear the commotion of his friends loading themselves into the lifeboat behind him. He hears Dustin and Lucas' halfhearted protests and Wills quiet pleas. The entire time he never lets his eyes leave hers. "They'll be safe?" he asks.

"Yes."

"Can you promise me that?"

"I promise," she says.

There is an assurance in her gaze that tells him to believe her and he finds himself doing so easily. He feels his shoulders relax and his lungs deflate, "Good," he sighs.

"—Hey! Stop, get back in the lifeboat!" the redhead yells behind them and Mike tears his eyes away from Jane's to spin around. He watches as Lucas pushes past the woman, grabbing one of her sheathed swords and running towards Jane with look of pure rage.

"Let him go!" Lucas screams, winding his arm back to take a deadly swing at Jane. Mike tries to speak up, to tell Lucas to stop, to tell him to get back into the lifeboat and _leave _while they still could. But he can't. The words are frozen on the tip of his tongue. He does nothing.

He does _nothing. _

In a terrifying suspended moment, Lucas' eyes widen, the sword drops from his hand, his feet stagger backwards and the dark-haired woman stands in front of him with her sword drawn and stained red. Lucas looks down at his abdomen while his pale shirt turns a deep shade of red. He looks up at Mike, their eyes locking for a single second, before he falls down.

"LUCAS!" his name practically bursts from Mike's chest, ripping through the air like thunder. He can hear Dustin and Will yelling in the background, but he can't make out what they're saying. Perhaps it's the shock mixed with fury that causes Mike's mind to act on its own accord, but he lunges forward and reaches for the gun that's holstered at Jane's hip. He pulls it loose from its hiding place and aims it dark-haired woman. She looks at Mike and the weapon in his hand, attempting to hide her panic, but Mike sees the way her confidence wavers.

"You," he says accusingly, his voice dipping low, "You _killed _him."

The woman doesn't say anything, she only stares back at him in quiet analyzation.

"Michael," he hears from behind him and he whips his head towards Jane. Her eyes still cold and void of emotion. Not even the slightest hint of guilt. And after what they just did?

"You_promised _me," he says, keeping the gun aimed at the dark-haired woman. "You said they'd be _safe._ You _lied!_"

"You friend running at me with a weapon drawn was not a part of the deal," she said evenly, "That changed the situation."

"Bullshit!" he yelled, turning to look at the dark-haired woman again. "You just killed an innocent man!"

Mike can see Jane take a step closer to him out of the corner of his eye. "So, are you going to shoot her?" she asks, "She was just acting in self-defense."

Mike cocks the gun, a familiar _click _cutting through the air. "She _killed _him," he repeats with a cracking voice.

"Will that make you feel better?" Jane asks, "Revenge?" the words feels heavy on her tongue. As if it's a question she's tired of asking.

Mike feels his finger hug the trigger, brushing it carefully before slowly squeezing it. _She killed him_, he tells himself. _She deserves to die, _he thinks. And he wants to do it. He _really _wants to do it. He wants to take her life away just like she took Lucas'. But as much as that unyielding desire tells him to _pull the trigger, _he can't.

Killing her won't bring Lucas back.

Killing her won't let Dustin and Will leave.

Instead he lowers the gun, rushing to grab the sword that had fallen from Lucas' hands, and then running towards the lifeboat. He catches Will and Dustin's eyes, both glassy and grief stricken—probably similar to his own. They're talking to him, trying to tell him something, but he can't hear them. Instead, he swings his arms back, gripping the sword tightly, and slicing the rope to the lifeboat clean through. He watches as they fall downward into the sea below.

He drops the sword to the deck with a _clank. _"There," he says simply, still tightly gripping the pistol in his hand. He turns back towards Jane and the dark-haired woman while the redhead draws her other sword and aims it at Mike. His eyes fall to the ground where Lucas lays, a dark pool of crimson surrounding him like a hellish halo. "But one more thing," he says, pulling his gaze away from the awful sight and looking back to Jane.

He cocks the pistol again pulling it upwards. It has a weight to it now that he didn't feel before, as if it had somehow gotten heavier in the brief time that he had been holding it.

"Hey! Put the gun down!" he hears the redhead yell beside him, but he doesn't listen. He brings it up past his waist, past Jane and the other woman, and lets the barrel land just under his chin.

And in the moment before he pulls the trigger, he swears he sees her stony eyes crack.

* * *

**Yeah, that was much more dramatic than I intended, but now everything is set up correctly and I can get into what I want to get into. Maybe enemies to lovers? Idk... Mileven's ****obviously endgame tho in this. Also DW no one dies, okay? I'll spoil that for ya'll if you care to read this A/N. Let me know what you thought! 3**

**-LovelySheree**


End file.
